


Bandits

by luciblue



Category: The West Wing
Genre: Ass Play, F/M, Fluff, Fluff and Smut, Plot What Plot/Porn Without Plot, Porn, Romance
Language: English
Status: Completed
Published: 2020-09-22
Updated: 2020-09-22
Packaged: 2021-03-07 18:40:50
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,914
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26602363
Author URL: https://archiveofourown.org/users/luciblue/pseuds/luciblue
Summary: Toby has a goal in mind, will CJ agree or really: did I just write 5K words about anal sex?ENJOY THIS PORN
Relationships: C. J. Cregg/Toby Ziegler
Comments: 1
Kudos: 1





	Bandits

**Author's Note:**

  * For [cantbebovvered](https://archiveofourown.org/users/cantbebovvered/gifts).



> Originally written for cantbebovvered, whom I adore!

i.

In one brief moment, Toby decided to throw caution to the wind. It was early morning on a Sunday - their one real day off during the week - and they’d been back together for a little over a month this time. He wondered how he could have been apart from her for so long. The sun had just risen, and the room was cast with subdued glow. 

They were naked and sleepy, her warm body pressed up against him, a leg thrown over his, kissing sloppily. Toby felt like he was floating on a cloud. Running his hands up and down her back, Toby then reached to grab CJ’s ass and pull her closer to him, but instead of running his hands further down her miles of legs, Toby had another idea. As he continued to stroke her bottom, Toby slid his fingers into the cleft of her cheeks until he reached the swell of her wetness, and stroked back up in between her cheeks again. Finding no signs of protest, Toby continued this process until CJ’s small, tight back entrance was just as slick as her front, as he massaged her pussy and ass. 

“Does this feel good?” he whispered in a low, gravelly tone. 

“Mmm,” she nodded, looking up at him with bedroom eyes. “Yes. I want you inside me,” she replied before capturing his mouth with hers as she climbed on top of him. 

He could feel the heat of her pussy on top of his rigid dick, and slipped easily inside. Toby gave up his exploration and got lost in the sensation of being buried inside her, but as she lazily writhed against him, he hoped this was only the beginning of something bigger. 

Ii.

As they exited the elevator on her floor of her apartment building, Toby’s cock became half hard as he watched CJ sashay down the hallway, sheathed in the most beautiful sequined ball gown he’d ever seen her in, her back muscles flexing as she walked. 

CJ looked over her shoulder to see Toby’s eyes cast down, looking at one thing and one thing only.

“Do you like what you see?” She asked flirtily, continuing her strut to her apartment. 

“Is that a rhetorical question?” He chuckled as he embraced her from behind while she fumbled with the keys to her door. She dropped her keys twice as he peppered the back of her neck with hot kisses. 

After they got inside, CJ pushed Toby against the door and kissed him deeply, while her hands flew to his belt buckle. Before he could say, “super conductor supercollider,” he found CJ kneeling before him, her tongue flattened against the other side of his now rock-hard cock, licking him like the best ice cream cone she’d ever had. Toby threaded his hands through her blond strands, moaned, and let his head fall back against the door. Her mouth felt like a miracle. 

While he was able to withstand a few minutes of her relentless, delicious sucking, her hot mouth and tongue doing their best to milk his orgasm from him, Toby had to admit defeat. A few more minutes and she would have been successful, but Toby wanted to come inside her. He gently grabbed a fistful of her bob and pulled her delicious pout off his throbbing, swollen penis, pulling her head back to look into her eyes.

“I’d like to come inside you. Do you want that?” He asked her, panting, looking into her hooded eyes. 

She kissed the tip of his cock with her lips and stood up. As she moved to undo the straps of her dress, Toby shook his head. 

“No. Leave it on. You look too good in it,” he smiled warmly. 

He took her hand and guided her to the edge of her couch, where he spun her around and began to kiss her neck and shoulder, holding her back tightly to his chest. 

“Stay just like this,” he whispered, as he leaned down to gather the bottom of the dress up from the floor. He pulled her tiny thong down to her heels and she stepped out of it. CJ leaned over the arm of her couch, which was big and round and perfect for this exact situation, providing her with the right amount of support. She gathered pillows to support her head and neck, allowing her to focus on Toby’s ministrations. 

Toby found himself on his knees face to face with both of CJ’s beautiful entrances. He kissed the outside of her vulva lightly, and then allowed a small exploratory lick to taste her wetness, garnering a sigh from his partner. She spread her legs wider. 

“Your mouth feels so good, Toby,” she moaned. 

Toby began to lick fat stripes from her clit to her perineum, making his licks longer and longer, until his tongue reached her asshole, which he licked lightly. 

CJ let out a harsh breath. “Toby, I--” she gasped. 

“Should I stop?” He asked earnestly, his hands on each of her cheeks. 

“No! No, I -- what are you doing?” Her hesitant response was laced with dark curiosity. Her head remained on the pillows, eyes snapped shut. 

“I’m licking you. All of you. Does it feel bad?” Toby stroked CJ’s hindquarters with his palms and gave her ass a small squeeze. 

“No, just, I’ve never had…that...there...” she paused. “Is it okay for you? I mean - do you like it?” She eked out, hesitantly. Her head peeked up from the pillows. She bit her lip. 

“More than okay - do you like it?” he peppered her cheeks and the backs of her thighs with light kisses while he waited for her to respond.

“Um. Yes? I think so...” She put her head back down and pushed her pussy out to him. 

“You’ll tell me if anything doesn’t feel good?” he asked, almost directly into her folds, continuing to plunder her pussy and ass with his mouth. 

CJ felt her thighs begin to shake as Toby began to focus solely on her ass with his mouth, his thumb inside her pussy, pressing on her g-spot, and his two fingers gliding deliciously around her hardened clitoris. 

“Toby, oh my god,” she breathed, clutching the pillows beneath her upper body. 

“Do you want to come?” he asked, the tip of his tongue pressing insistently on her tight rosebud. 

“Ohh! - oh, fuck. Oh fuck - !” was about all she was able to get before her pussy began to pulse around his thumb. She felt her orgasm come from another part of her, entirely - radiating up her back and down her thighs to her heels, still encased in her stilettos. 

Toby stood up and stroked his cock. “Do I have you for one more?” he whispered in her ear seductively, his body covering her back, his chest hair deliciously itching against her skin. Thank god for low backs on dresses. 

“Please,” she whispered, begging, rubbing her ass against the apex of his thighs. 

Toby entered her gently, intertwining his fingers with her as he pumped into her slowly and surely, being aware of her sensitivity post-orgasm. As soon as he felt her push back against him, meeting him thrust-for-thrust, Toby moved up to grab her hips and drive his cock deeper into her. 

She felt so hot and good, so warm and wet around him. As he crooned and moaned about how good she felt, Toby took his thumb to rub lightly against CJ’s tiny rosebud, which was staring up at him as he stroked her cunt with his penis. 

“Toby --” she warned. 

“Too much?”

“No, no - don’t stop - I’m going to --” 

“Come with me,” he pleaded. 

Toby felt CJ begin to unravel. As she came, he felt her ass open with her contractions, allowing just a bit of his thumb to slip inside her ass. 

Iii.

They’d been playing cat-and-mouse for weeks. Toby was certain CJ enjoyed having her ass played with, but she never explicitly asked him to touch her there. More often than not, she positioned herself in ways for her ass to be touched, whether it was on top of him and moaning assuredly when his hands crept down between her cleft, or positioning herself head down ass up, impatiently waiting for him to enter her while she fingered her clit. Every time his finger or tongue slipped inside her hole, she cried out in immense pleasure. 

She came harder than he’d ever remember her coming before. It turned out she was a complete ass bandit, he chuckled to himself, but she just wouldn’t talk about it. And it actually made sense to him - her playing coy (press secretary after all), making him draw his own conclusions and forcing him to speak up (communications director, duh). 

One night after a particularly satisfying round of sex, Toby finally broached the subject. She was curled up against him, just how she was that first time he touched her there, her leg thrown over his, her pussy close to his softening cock as it slowly slipped out of her. 

“Have you noticed anything different about our sex life these last few months?” He asked, stroking her sweat-matted hair away from her forehead.

“What are you getting, at Toby?” She cocked her head at him and smiled.

“This,” he said knowingly, as he reached around and stroked her ass, looking her in the eyes, his eyebrow arched. 

CJ blushed. 

“I have to admit,” Toby continued. “I’m very glad you’re enjoying it,” He took a beat. “I’m asking because I want to make love to you this way.”

CJ remained silent, her head nestled between his shoulder and neck. 

Toby continued, “are you open to the idea?” 

As CJ spoke, her head turned towards the pillows, her voice growing fainter.”

“Oh. Um. Maybe? I - I’m not entirely opposed I just...Toby - how, exactly would you be able to get inside? I mean...you are a lot bigger than a finger.” 

“Well…” he began, continuing to stroke her hair, “This,” he said, pressing gently against her tight hole, “is a muscle. So just like dancers train for flexibility, we’d have to get your body to do the same thing. Train you to take me. Does this sound like something you would want to try?”

CJ sat up stared at him, approximately one third embarrassed, one third intensely curious, and one third unbelievably aroused. She held him at arms’ length. 

“Train me?” she breathed, wide-eyed. “Like I’m some kind of animal? Wait. Are you speaking from experience?” 

“Not entirely...ok, a little - and no - are dancers and athletes dogs? Come back here,” he said, tugging her back to him, “I could do some reading up on it; we don’t have to do anything you’re not comfortable with.” He continued staring at her shoulder, where he was stroking her with his fingertips. 

CJ waited a moment before responding, her face nestled at the junction between his neck and his shoulder. “I need to think about it, but this isn’t a no. Let’s go to sleep. I love you.” 

iv. 

Over the next few weeks, Toby and CJ continued to tease and tempt one another regarding her ass. Toby relished how much pleasure he was able to bring her, and was excited about the potential to be closer to her in a new way.

Toby was diligent in his research. He read sexual health and educational blogs, and bought a book called “The Ultimate Guide to Anal Sex for Women,” which he eventually shared with CJ by hiding it in her nightstand after he read it. He learned all about a woman and her connection to her ass, which was different from a man’s, but no less pleasurable, wired with many nerve endings. He learned how to make anal sex - which if done wrong, could be painful - the most comfortable, safe, and enjoyable experience for her. Particularly, he was intrigued by just how wild anal sex could make a lot of women. Primal was a choice word for it. 

After intense research, Toby went online and purchased some toys to help CJ be able to take him. He carefully chose several graduated anal plugs, a dildo slightly smaller than his own penis, to help her get used to the sensation, and a vibrator, to help keep her stimulated in case of any minor discomfort. He just needed a plan to introduce them to her. 

v.

Toby didn’t tell CJ about the toys he had acquired until several weeks later. It was Saturday night, kicking off their one day weekend. They’d finished dinner long ago, and were curled up on the couch watching TV, or rather, making out like a couple of teenagers with some medical drama on in the background, long forgotten. Knowing CJ would be worked up and eager, Toby decided to hedge his bets and broach the subject, knowing it could shut down the ensuing activities. 

“Do you remember that conversation we had several weeks ago?” He asked her, his voice deep and sexy, stroking her back.

CJ let out a little giggle and blushed, like they were talking about something absolutely verboten. She nodded. He took it as a sign to continue.

“Well, in addition to that...reading material I shared with you, I also took the liberty of buying some toys for us. Do you think we could try one tonight?”

CJ blushed further and looked down at her hands, holding his, in her lap. 

“I want it,” she said, quietly, and squeezed his hands. 

“Oh?” was Toby’s response.

“Yes,” she breathed. “I want to experience you in me, in that way. I want to try. I’m a little nervous, but I’m also excited.” 

“Come,” he said, and led her by the hand to the bedroom.

Toby lay CJ down on his bed and undressed her before undressing himself. He held her close and snaked his hands down between her legs - he had read that by orgasming first, a woman would be more relaxed and ready to be penetrated anally. He went slowly with her, not wanting to rush, running his fingers lightly up and down her outer folds, and finally slipping in between her labia to feel her wetness. CJ spread her legs wider, wantonly. 

It was not difficult to make her come. He had studied her, asked her, begged her to tell him how to make her feel good, to make her come apart. And so she did; Toby had always been an A+ student. After she came down, Toby went into the bathroom to bring back his purchases. The first was a small anal plug, no bigger than a finger and a half, and a quality vibrator. 

CJ’s eyes were wide as she said, “Oh Jesus, Toby - do you think that’s going to fit in me?”

Toby laughed and smiled, “I’m going to try and put this inside you very slowly. We can stop if it starts to hurt and maybe you won’t be able to take it all tonight. You can use this vibrator on your clit to help keep you relaxed. You’ll tell me if anything feels wrong or hurts?” 

CJ nodded. Toby suggested that she lay on her stomach with pillows under her hips, to help provide access to her ass while keeping her relaxed. After she lay down, Toby began to kiss her thighs and bottom cheeks, and finally licking her hole, driving her desire to have something in her ass. He felt her shift to put her fingers on her clit, which she rode to increase the pleasure she felt from his tongue. 

When he felt she was ready, Toby retrieved the small plug and poured a substantial amount of lubricant in his palm, warming it up as best as he could. He dribbled some into her cleft, and took his finger, pressing some of the lube inside her. CJ sighed and pressed back against his hand. 

“Ready?” he asked her, lovingly.

With her affirmations, Toby placed the front of the plug against her ass and pushed gently. He heard CJ’s sharp intake of breath, and handed her the vibrator.

“Don’t forget this,” he reminded her, and placed a kiss between her shoulder blades. 

With the vibrator firmly nestled between her lips, Toby began to push again. CJ cried out just as the most flared part was about to enter her.

“Stop!” She yelled out, breathing harshly. She slumped over to her side in the fetal position. Toby discarded the plug and moved to curl up beside her, holding her tightly. 

“Did I hurt you?” He asked, rocking her. 

“I know you didn’t mean to.” she said quietly, her breathing still harsh. “I just want to go to sleep,” she whispered.

“Ok,” Toby responded, stroking her hair and kissing her shoulder. He shut out the light and let her drift off to sleep. 

When Toby awoke the next morning, he was alone. His heart sank temporarily, thinking she had left because of what had happened last night, until he heard the clinking of coffee mugs emanating from the kitchen. Relief washed over him. 

He padded out to find CJ in her robe with nothing else on underneath, sipping a cup of coffee, robe loosely tied and barely covering her. Toby moved to embrace her, and she welcomed his affection. He held her close to show her how much he cared, to show his protection of her. 

“Would you like some coffee?” She asked, after a moment. Already knowing the answer, she turned around to reach for a mug. As she poured coffee for Toby, she felt his lips at the juncture of her neck and shoulder, his hands at her hips, stroking. She let her head fall back onto his shoulder, allowing his hands to wander over her breasts and belly, pinching and stroking lightly. She allowed him to take her robe off, letting it pool on the floor, as his hands traveled to the apex of her thighs to tease and test her waters. Toby continued to enjoy her body, which soon became putty in his hands. 

Toby knew he was taking big risks at this moment that could get him in deep trouble for pushing boundaries. He knew that the minute she was uninterested he would stop, giving himself permission to help CJ push past her fear and into something he knew would be good for the both of them. He found himself on his knees in front of her ass and began to gently lick her; he would do it for as long as it took and as long as she wanted. 

Toby felt CJ bend forward and spread her legs, allowing the hands that had been holding her cheeks apart to wander. He licked her gently, his hands rubbing lightly against her clit, feeling it grow hard and big. Making a V around it with his middle and index fingers, Toby began to rub surely and firmly along the sides of her clitoris, feeling her legs begin to shake as she unraveled. Toby was incessant in his sliding against her clit, which had become hard and erect. He used his tongue to press against her hole, massaging it and relaxing it, hoping it would open up for him later. CJ began to unravel, feeling tingling radiate from her hindquarters outwards, all the way to the crown of her head. She sunk down to her knees after she came and leaned back against Toby, breathing hard. 

“I want you,” she breathed. “Take me to bed.” 

In bed, Toby covered CJ’s body with his, kissing her passionately, revering her. He began to stroke her pussy, moving to her ass and back up, pleasuring everywhere between her legs, trying to connect the pleasure of her ass to the pleasure of her cunt. With one hand, Toby placed his thumb against CJ’s clit and began to lightly rub, being mindful of potential sensitivity from her previous orgasm. He began to lightly tease and probe her ass with this other, stroking in and out gently, fingering her gently. He tentatively added another finger when he felt she was ready, allowing her to absorb the pleasure gradually. 

“Do you think you might like to try the plug again? You have two of my fingers inside you now. I wish you could see it. You turn me on so much.”

CJ was in a daze, her ass full of Toby’s fingers, her clit being thumbed lightly, keeping her engaged in pleasure without rushing her towards the edge of the cliff. All she could do was nod. 

Toby retrieved the plug and vibrator from from the nightstand after slowly pulling out of her. 

What Toby was rewarded for his patience with was possibly the most filthy thing he could have ever imagined doing with another woman. As he pressed the toy lightly against her rosebud, he successfully watched her ass swallow the small toy, his cock at full attention as it disappeared. He could see the flared edge nestled in between her cheeks, her pussy open and empty peeking out above, her labia receiving attention from the vibrator as she worked it up and down her vulva. He couldn’t remember being this hard in a long time. 

CJ breathed harshly, her eyes shut tight, her lip curled in what looked like a mixture of pleasure and pain.

“You okay?” He asked, concerned.

“Um, Maybe? I - stings a little, but okay, I think?” she said quickly and intensely.

Toby caressed her legs’ hind quarters. “Let’s give you a minute to adjust, just focus on your clit. What do you feel?”

“I feel…” she began, and trailed off. Toby could see the changes in emotion run across her face as her eyes opened. Bewilderment tinged with excitement. CJ drew in a big breath. Instead of answering Toby’s question, CJ leaned up on her arms, and pulled Toby on top of her. She kissed him passionately and sloppily, showing Toby exactly how she felt: ignited, turned on, ready to go. 

“Will you go down on me?” she breathed, looking him in the eye. Toby had never seen anything sexier in his life. 

As the weeks drew on, and with much patience and preparation, CJ graduated to the largest plug Toby had purchased. It had made its way into their lives several times a week: CJ wore it while blowing Toby and while he pleasured her with his hands and mouth. CJ began nearly every lovemaking session by placing whatever plug she was used to wearing in the palm of his hand, and Toby would place it inside her, almost like a signal that they could begin. Having her ass stimulated and full made her crave sex more often; it was on their minds most of the time from then on, even when it wasn’t supposed to be. The trust between the two of them deepened their love for one another; him learning how to pleasure something so completely new to the both of them drew them incredibly close. 

He especially loved her wearing it when he fucked her; it made sex more sensitive for both of them - she was so tight and because he could feel the nub of the plug rub his cock as he was inside her. Not only did she come so hard, oftentimes her whole body shook with the intensity of her orgasms, his cock insistently pressing upon her g-spot. He had never been one of those guys interested in sleeping with virgins once he was beyond the age of 20, simply because he didn’t particularly like the idea of trolling for super young women to fuck, but he had to admit that with the plug in, CJ certainly felt like one, and he was deeply, deeply grateful for it. 

vi. 

Toby rubbed the plug against CJ’s ass and pressed it in. When it was halfway through, he decided to try something new, and withdrew the plug. CJ looked over her shoulder at her lover and pressed her ass back, begging him to fill her. Slowly, Toby began to stimulate fucking CJ’s ass with the plug, and she began to move with him.

“You know, there’s one thing we haven’t yet tried.” He said, as he soothed his hand down from the base of her neck to her ass. 

“Oh my god, you mean?” 

“Yes, do you want me in your ass?” His voice was low and deep, and his hand stilled at her hip, caressing her waist.

“Oh god. Yes. Do it.” She said, decisively, almost impatiently. 

Toby’s cock twitched like he was 15 again. He grabbed the lube, pouring large amounts into his hand and on her ass, slathering it over her in excitement, trying his hardest to keep his cool. CJ flipped over onto her back. Toby kissed her deeply and excitedly. He reached for the vibrator and put it in her hand. 

“If you want me to stop, just say so, ok?” CJ nodded in affirmation as they both moved to put pillows underneath her hips to help give Toby better access to her bottom. 

Toby lined his cock up to her entrance. CJ switched on the vibrator and began to run it up and down her labia in anticipation, looking down at the junction between her thighs, to watch Toby’s cock enter her somewhere completely and totally different. 

At first, it almost felt like too much - his cock was bigger than the largest plug they owned by almost half an inch - and Toby could see the intensity of the sensation in her eyes. He paused. CJ shut her eyes, put the vibrator directly on her clit, and let out a harsh breath.

“Too much?” he asked. 

CJ nodded, but pressed her hips forward. “It’s ok. Keep trying,” she whined, impatiently. She was familiar with this practice, and knew a little bit of discomfort was necessary for such a big reward. 

Toby pressed again, more firmly this time, and felt the head of his cock slip in past her muscle. 

CJ pressed her lips together tightly. 

“Hang on for just a minute, breathe, if it doesn’t stop feeling bad in 30 seconds, I’ll pull out, ok?” 

CJ nodded rapidly and began stroking her clit up and down with the vibrator, easing the discomfort she felt, her ass more full than it had ever been, stretched to the max around the head of her lover’s cock. 

CJs breath began to deepen as he felt her relax around him, more pleasure taking over from the vibrations of the toy on her wet cunt. 

“OK?” Toby asked, trying to hang on with his head being squeezed the hardest he’d ever felt anything around his dick in his entire life. 

“More,” she breathed, and Toby slid in slowly, all the way home, until he was buried to the hilt inside her. 

“Ohhhh, fuck, Toby. Oh god. You’re totally in my ass.” Her lip curled, mouth opened wide; her teeth were exposed. She began to slowly rock her hips. 

“I am. You feel - I - wait,” he begged. “Wait, wait. Give me a minute,” he breathed, his forehead pressed against hers. Her ass gripped him so forcefully it felt like it was his first time all over again. He didn’t want all his labor to be wasted without giving her pleasure.

CJ switched off the vibrator - she didn’t want any distractions from any new sensations she felt. Toby put his arms underneath her knees, her legs spread wide, her ass full of his cock. Toby began to slowly rock against her. It was all they could do, any further movement and it would be game over for the both of them. He felt so incredibly close to her, it felt appropriate to move slowly as he made love to her ass. He began to withdraw a bit more with each stroke, still moving slowly, both of them climbing higher with the sensation of him stroking her hole. 

CJ’s orgasm snuck up on her quickly - she was unused to coming solely from her ass - and it came on like a train with broken brakes barreling down the tracks. Her orgasm made her feel holy and ethereal: complete in a way she had never been before, revered and special. Her ass gripped onto Toby’s cock tightly, pulling his orgasm out of him and milking him of his come. As she felt him pulsing, felt his come press against the walls of her ass, CJ’s hands flew to her clit to help her stutter into another final orgasm, the two of them shouting in unison, one being together as he emptied himself into her with everything he had. 

“Holy shit, CJ. That was…” he trailed off.

“I know. What the fuck?” She laughed. 

Toby slipped out of her. 

“What did it feel like?” he asked her. 

“It’s so hard to describe - it’s almost like I had a different orgasm entirely. It was unreal, I wish you could experience it.”

Toby gathered her in his arms and kissed her deeply, before she pulled away and looked into his eyes with a devilish grin on her face. 

“Oh wait,” she said, a laugh beginning to build. 

CJ rolled herself on top of Toby and pressed her sex into Toby’s while she kissed him deeply. 

“What?” Toby asked, genuinely curious. 

CJ looked like the cat that ate the canary before she responded, “You totally can experience it. In fact...I think it's your turn now.” 

THE END.


End file.
